Chemoenzymatic approach to optically active 4-hydroxy-5-alkylcyclopent-2-en-1-one derivatives: an application of a combined circular dichroism spectroscopy and DFT calculations to assignment of absolute configuration.

Abstract:

:A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated electronic circular dichroism [ECD] and vibrational circular dichroism [VCD] spectra) to determine the absolute configuration of both stereogenic centers in 4-hydroxy-5-methylcyclopent-2-en-1-one was demonstrated. It was also demonstrated that the concurrent application of ECD and VCD spectroscopy can be used for the determination of the configuration of two stereogenic centers.

journal_name

Chirality

journal_title

Chirality

authors

Frelek J,Karchier M,Madej D,Michalak K,Różański P,Wicha J

doi

10.1002/chir.22322

subject

Has Abstract

pub_date

2014-06-01 00:00:00

pages

300-6

issue

6

eissn

0899-0042

issn

1520-636X

journal_volume

26

pub_type

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